Lubricating oil



Patented Apr. 1, 1941 UNITED STATES IPA-TENT jor ricn 2, 36,896 rename-ruse on.

rayon Davis, Bert 11. Lincoln, and Gordon D. I Byrkit, Ponca City, Okla, assignors to Continental Oil Company poration of Delaware Ponca City, kla., a cor- No Drawing. Application September 19, 1938,

Serial No. 230,660

reclaims. (Cl. 252-52) Our invention relates to. improved lubricating oils and more particularly to lubricating oils having exceptionally high viscosity indices.

Two general methods of obtaining high viseosity index oils have been described in the-literature of the art, namely, the production of synthetic or synthetically treated oils with high.

viscosity index and theaddition of various materials to ordinary or low viscosity index oils to improve them. Our products are of the first type and are intended to be used directly as lubricating oils.

In the prior art of synthesizing oils of lubrieating properties, various processes have been employed as well as various starting materials. For example, lubricating oils have been prepared by the action of polymerizing reagents such as aluminum chloride, ferric chloride, phosphoric Other objects of our invention will appear in the course of the following description. g

Briefly .our invention consists in the production of mixed cyclic and alkyl ethers of the type ROE in which R is a high molecular weight, aliphatic' radical having at least 13 carbon atoms,

such as may be' obtained, for example, from paraflin wax and R is an organic radical containing a carbocyclic or heterocyclic nucleus which may or may not bear various alkvl orother substitutinggroups. It is necessary to have at least 13 carbon atoms in the aliphatic radical in order to obtain as products lubricating oils having viscosities of at, least 50 seconds Saybolt at 160 acid and phosphates, boron fluoride, and the like v on lower olefins such as ethylene, propylene, bu-

tylenes, and higher olefins such ashexene, octene, and even cetene, CmHzz. Various mixed olefins have been polymerized such as cracked gases, cracked paraflin wax and the like.

' Synthetic'lubricating oils have been prepared by various condensation reactions. For example, thecondensation of halogenated wax or other netroleum fractions with aromatic hydrocarbons or other aromatic compounds such as naphthalene; di-phenyl ether and-the like.

The products of our invention are more'cheaply and easily-.-made than other synthetic lubricating oils. They have higher viscosity indices than any previously reported. Furthermore, we utilize non-lubricating fractions of "petroleum to produce these high quality lubricating oils. Our

degrees F.

While ordinary lubricating .oils have viscosity 'indices from as low as --40 for naphthenic oils to 90 or 100 forPenhsylvania oils, .theproducts of our invention haveviscosity indices of not less than 90;

The aliphatic radicals of our products may bederived fromany source and may be of various degrees of purity, that is, freedom from other 'types of radicals. For example, cetyl chloride is a suitable source of the cetyl radical. We may utilize parailin hydrocarbons of various petro leum fractions as sources ofcaliphatic radicals products are, like the so-called white .oils, .ex-

tremely, stabletoward oxidation and sludging which is not true of ordinary lubricating oils. By our processes, Weconvert materials of low economic value into products of greatly enhanced value. i

One object of ourjinvention is to provide lubricating oils having extremely high viscosity indices.

Another object of our invention is to utilize nond'ubrlcant petroleum fractions to produce improved lubricating oils.

v A ,iurther object r our invention is to syn- ,theslze materials which may be used to improve the characteristics of ordinary lubricating'oils.

A still further object of our invention is to convert materials oflow economic value into valuable products by a commercially feasible process.

found'that these productsof chlorination are very crude mixtures of the chlorinated hydrocarbons and contain unchlorinated hydrocarbons and the mono-, di-, and polychloro derivatives. The whole "mixture cannot be considered the desired-compound. For example, a so-called trichloro paraffin wax", containing 2 4 percent-chlorine, which corresponds very closely to the percentage of chlorine in the trichloro compound, .was separated by means of crystallizationfrom acetone at low temperatures. The least soluble.

portion consisted ofunchlorinated wax. The next least soluble portion consisted of a mixture of monochloro 'wax' and unchlorinated wax. The percentage'ofunchlorinated wax in the original chlorinated waxes.

mixture, supposedly"tri chloro paraffln wax," was found to be 7.2 percent. Thus, evena trichloro parailln as so-called' in the prior art, because of. the total chlorine content, was infact a crude mixture containingas much as 7.2 percent of" unchlorinated wax and quantities of monoand di-chlorowaxeaas well as trichloro wax and more highly chlorinated waxes. Its-use would not give the same results as a trichloro free of higher and lower chlorinated parafiin,

since the products will contain unhalogenated par hydrocarbons and mixed derivatives.

. Even though'the appropriate amount'ofchlorine isintroduced-in the wax toform a monochloro wax, we have found that the crude chlo-.

rination mixture contains, in addition to small amounts of chlorine and hydrogen chloride and the desired monochlor wax,' also unchlorinated wax and more-highly chlorinated waxes. When dichlor and higher chlor wax is the desired product, the crude chlorination mixture 'will contain in addition to chlorine and hydrogen, less highly.

In contrast to the use to obtaina relatively pure monochlor compound free from unchlorinated hydrocarbon and free from morehighly chlorinated compound.- Wemaythtis prepare -(1) monohalogenated hydrohydrocarbons and more highly halogenated hydrocarbons'; (2) dihalogenated' hydrocarbons substantially free from unh'alogenated hydrocarbonsand monohalogenated hydrocarbons, as well as from halogenated hydrocarbons containing more than twoatoms of halogen per molev of .a mixture, we; have 'foundit possible, as fully described below,:

-. carbons substantially free from unhalogenated clue; and (3) trihalogenated hydrocarbons free fromhalogenated hydrocarbons containing fewer orniore than three halogen atoms per molecule and'free from unhalogenated hydrocarbons. We Jre'fer in this specification to these materials as carbons from such sources as the heavy ends of gasoline, kerosene and the like, we preferably use chillingonly as a method of separation-since range as unhalogenated'. higher boiling. hydrocarbons in the same fraction of starting material.

The unchlorinated wax separated from the crude chlorination mixture may be recycled to the chlorination step to obtain further quantities of chlorinated waxes. It does not represent refractory material, and the same proportions of -chlorination products are obtained from it-as 2 from fresh wax. r

The liquid chlorinated waxes after separation of unchlorinatedhydrocarbons consist largely of monochloro and dichloro, waxes when approximately or 20 percent chlorine, respectively is introduced into a starting wax, of,say', from 115 to 130 F. melting point, but some polychloro wax may be present... These monoe and dichloro waxes may be separated from each other by crystallization from acetona'using a solvent-'chlor waxratio of from 1 to 1 to 20 to 1. In preparing the solution, an elevated temperature may be employed to insure that the chloro waxes are com-- pletely dissolved in the solvent. The solution is then chflled to. a 'temperature of between minus F. and minus F. when a parafiin waxof 115tq 130 F. melting point is used for the initial I chlorination. The monochloro waxes are precipitated out nearly quantitatively, while the direlatively pure monohalo'gen compounds, rela tively pure dihalogen compounds, etc.

The chlorination ofmost petroleum hydrocarbons. lowers their-melting points and, up to a certain point, the greater theextent of onion-- nationr that. is, the more chlorine atoms per molecule, the lower the melting-point... The decrease inmelting point is stepwise, and this per- :mits usv to separate th'e'unchlorinated hydrocaro bons from the monochloro hydrocarbons and the monochloro hydrocarbons from the dichloro and higher chlorinated-hydrocarbons. we 'can, for example, separate theunc'hlorinated wax from the air-blown "mixture by filter pressing at such temperatures that all',of the chlorinated waxes are largely liquids, while the unchlorinated waxes are largely solid.v The temperature-for the pressing operation will depend; of course, on-the char acter of the wax used'initially and will'vary con siderablydepending'on this factor. For example, at-a temperature of from 80F. to 90 F. the

- monochioro product formedby the chlorination of having a melting point of 120 I".- will be liquid,' while wax ,will be solid,

enabling a ready separationto be eflected. l ofaeparation, as for example,

I. belective solvent extraction at various j 'tanperatures, .thouseof diluents followed by chilling settling or filtering, and the like, my

' 'chloro and polychloro' waxes will remain in solution. The precipitated monochloro waxes may be readily separated by settling, filtering, or centri fuging.

i We haveals'o vents such as methyl-ethyl ketone, acetone, benzene, methylene chloride, various other halogenated" solvents as well as liquid propane orv butane.- Mix-tures of-two or more solvents may:

be used. The use of'a particular one or combination of.-these solvents requires the'experimental determination of the proper proportions and temperatures necessary to obtain the desired separation of the crude chlorination mixture into the various stages of chlorine contents. Halogenated solvents serve to aid in the precipitation 'of unchlorinated wax, while benzene and hydrocarbon solvents increase the solubility of the mor highly chlorinated materials. After removing the monochlor wax, the solution may be chilled to a lower temperature or concentrated by distillation or evaporation of the solvent or both to precipitate the dichlor waxes which may be then separated. A further separation of the remaining liquid may be accomplished by repetition ofthese processes. In this manner, thecrude chlorination mixture may be separated 'into u-nchlorinatedwax, monochlor be..eml !07ed vtor separating solid unchlorinated wax from chlorinated portions, and for separatchlorinat d'portions, and so oni In separating wax, dichlor wax and polychlor wax. We proved ample, by chilling until approximately half of the sample had solidified. Solid and. liquid portions were separated by a filtration and con! 12.1 and 11.4 percent chlorine respective- 17. v v I 1".-melti ng point, batches showed chlorine conrelatively pure monochlor, dichlor, eta, hydrotents of 19.2, 10.3'and 10.5 percent. These values In the case of the wax which had the used other crystallization solare ve y blose to the. theoretical of 10.0 percent. Thus, our relatively pure monochlor wax is submay be practiced on paraflln hydrocarbons of higher and lower molecular weight including all those parafiln hydrocarbons whose monochloro derivatives melt lower than the hydrocarbons themselves. While the product of the preferred embodiment of our invention is a mixture, the monochlor derivatives prepared according to our invention are free from unchlorinated and more highly chlorinated material. The dichloro derivatives are free from unchlorinated hydrocarbons, monochlorinated hydrocarbons, and, more highly chlorinated hydrocarbons. The purity of the final product with'respect to homologues is sulflte, sulfurousacid, potassium ess. It desired, chlorineanalyses may be conducted on samples of thematerial being chlobe given a stabilizing treatment with .dilute aqueous solutions of sodium sulfl'te, sodium bi permanganate, sodium hypochlorite, or the like. I

w As an example of the manufacture of a relatively pure chlorinated hydrocarbon, we describe here the manufacture of a relatively pure monochloro wax which contains-approximately 26 determined by the purity of thestarting hydrocarbon. It is understood, of course, that, when a pure hydrocarbon is employed, a correspond ingly pure halide is obtained.

Having s'electedthe hydrocarbon in accordance with the desired final product, we chlo-' rinate the hydrocarbon until approximately that amount of chlorine is absorbed which will .produce the monochloro compound when that is the desired product, or approximately that amount of chlorine which will producethe dichloro compound when that is the desired product, etc. In the case of parailln hydrocarbons having from 18 to 24 carbon atoms per molecule, that is, a material having a melting point of approximately 120 F., about will produce substanti y the equivalent of the v monochlor product. The amount of chlorination may vary between 9 percent and 12 percent without being disadvantageous. The percentage of chlorine introduced into the hydrocarbon justdescribed will be approximately 17 percent when a dichloro product is desired. The amount rcent added chlorine I carbon atoms per molecule. We started with 723.4parts of a hydrocarbon wax having a melting point of 120 F. The wax"was chlorinated until 72.5 parts by weight ofchlorine'had been absorbed. The chlorinated wax was airblown to remove hydrochloric acid and uncombined' residual chlorine, and then pressed at 85? F.. The linchlorinated wax was reserved forfurther chlorination. The liquid portion was then dissolved in'acetone, 350 parts of crude chloro "wax being dissolved -in 3,226 parts of acetone. The solution was chilled to .minus 18 F: and 185 parts by weight of solid monochloro wax containing 10.3 percent chlorine was-precipitated. Monochlor wax from this paraflln wax contains theoretically 10.0 percent chlorine. The monochloro wax was normally liquid at room temperature.

Dichloro waxes and polychloro waxes prepared according to our method are "suitable for use in of chlorine introduced will be less in the case of the high molecular weight, higher melting hydrocarbons, and more inthe case of the lower molecular weight, lower melting hydrocarbons, for a given number of chlorine atoms per mole- '-chlorinated wax or lower chlorinated.

any oi the applications described in the prior art, where such dichloro waxes and polychloro waxes are required. Since they contain no un waxes, they are particularly eflicient in ,these and are a distinct improvement over the prior art which used crude chlorination mixtures of approximately the proper chlorine content but which consisted of unchlorinated wax and more highly chlorinated wax. I

While chlorine has been referred to above almost exclusively, it is to be understood. that any of the halogens are suitable to make halogen derivatives 01' the paraflin hydrocarbons accord-' ing to our method. Thus bromine, iodine, and fluorine may suitably be used to obtain the corresponding bromides'iodides and fluorides. For some purposes to which the halides are to be put,

the bromine compounds are much to be desired cule, The chlorination may be accomplished in any suitable manner. We prefer to heat the hydrocarbon to a temperatureat least that of its meltingv point and pass chlorine gas through the melted hydrocarbon; Agitation increases the efilciency of chlorine absorption but is not essential. The chlorination reaction is exothermic and the heat of reaction is ordinarily ample to over the chlorine compounds, since they are considerably more reactive. Where this is" the case, we halog'en.ate with bromine, .using a halogen carrier, such as halides of antimony, phosphorus, iron, various metals, and thelike, and separate the brominated mixture into its components as described above-in the caseoi the chlorine com pounds. Theiodine compounds 01 the paraflln hydrocarbons may be' preparedby direct iodination or by an indirect method. By the indirect method, the above described separation of mono-, di-, and poly-halogenderivatives may be employed in any step of the process. Thus we may separate a relatively pure monoor dichloro paraffin and convert it to the corresponding iodine compound, or we may convert the crude halogenated mixture into a crude iodinated mixture and then separate into-the various. stages of halogenation. Fluorine may beintroduced into application's o -'chlorophenol,

paraflin hydrocarbons directly or indirectly by analogous methods. For most purposes, however,

1 we prefer to usethe chlorine compounds because above all the other halogens.

In'preparing .the lubricating oils of our invention, we .use these relatively pure monochlor .waxes or dichlorwaxes and treat them with of the cheapness. and availability of chlorine metal derivatives of cyclic hydroxy compounds.

We prefer to use the cheap sodium salts but other alkali, alkaline earth and heavy metal salts of 'alkyl group attached to the ring as in p-tert.-

butylphenol, 'octadecylphenol, pentacosylphenol, amyl cyclohexanol, and the like. Other substituting groups may be present as in p-nitrophenol, p.-, hydroxybenzaidehyde, amyl salicylate, p-hyviirbxyacetophenone, I o hyd-roxybenzophenone, phenol sulfonic acid, its salts, esters and amides, vanillin, eugenol, thymol, mesitol, carvacrol, I tri-iodophenol, phenol, nitrochiorophenols, o-methylaminophenol, picramic acid, vm-hydroxyazobenzene, thiophenol, selenocresol, resorcinol, hydroquinone monomethyl ether, o-chlorobenzyl alcohol, pheny'lethyl alcohol, cinammyl alcohol, and the like.

The reaction whereby ourlubricating oils are produced proceeds at satisfactory rates at about 200" C-. with most of the ring hydroxy compounds and most of the halogented aliphates, but temperatures between 100 C. and 300 C. ,may be used, provided the reaction is not too slow or provided the product is not converted to dark colored products of relatively low viscosity index.

r a viscosity index of 91.

pentachlcro- Example 2 A mixture of 108 parts of o-cresol and 44 parts of sodium hydroxide were melted together and heated at 110-140 C. for two hours, poured out on a cold surface and pulverized. It was substantially water-free. To this solid was added 200 parts of our relatively pure monochlor wax and the mixture was heated at 160 C. and then at 160-190 C. for one hour. Mixture was cooled, washed, steamed, and dried. It had a viscosity of 89.4 at 100 F. and 40.2 at 210 F. The viscosity index was 160.4.

Example 3 i phenol, 34 parts of potassium hydroxide and 3,000 1 parts of toluene were heated as described in Example 1 until no more water was formed. Then 232 parts of our relatively pure monochlor wax was addedand, after removing the toluene, the mixture was heated at 190200 C. for two hours. The oil obtained from the mixture as described in Example 1 was chlorine-free and had a-vis- It will be obvious that our relatively pure wax ,and metal derivative must be substantially dry in order to carry out this'reaction. We may use purchased dry'metal phenolates or alcoholates or they may be prepared and-treated with the halogen compound in the same reaction vessel. We mix the solid metal derivative with the halogen compound and keep the mixture agitated during the reaction- Usually the mixture is more .diillcult to agitate at first than after the reaction has prbceeded'for a 'tifiie.

We add water to the reaction mixture and "wash out metal halide and excess metal derivative from our synthetic oil. Usually the oil needs only to be dried and this may be accomplished in any suitable manner. For example, we may use a vacuum dehydrator.

The following examples are given as illustra tions and not' as limitations:

, Example 1 A mixture of 94 parts of phenol and-44 parts of sodium hydroxide in 300 parts of toluene was heated. "The condensate was separated, discarding the water. and returning the toluene to the reaction chamber. When no more water was separable from thedistillate, 200 parts of our relar tively pure monochlor wax was added and the toluene removed by distillation. Reaction temperature was held at 160,-180 C. for two hours.

Mixture was cooled and water added. Oil was washed several times with water, then with dilute acid and finally steamed to remove any phenolic After removing the solvent, the residual oil had cosity of 233.1 at 100 F. and 56.3 at 210 F. The viscosity index was therefore 148.1.

Example 4 heated for /2 hour with dilute hydrochloric acid and the organic product extracted with benzene.

a viscosity of 80.0 at 100 F. and 40.0 at 210 F. The viscosity index of this oil is 187.4.

Example 5 A blend of 40 percent by volume of the prod-- densation product had a viscosity of 141.3 seconds elat 100 F. and 43.1 seconds at 210 F. The viscosity index of the pale oil was 85 while that of the blend described was 110.7.

Examplefi We'may condense 130 parts of the anhydrous sodium derivative of benzyljalcohol .with 200 parts procedure of the preceding examples to obtain another product of our invention.

Example 7 when treated by the procedure of the preceding odor. The dried oil had a viscosity (S. S. U.) examples gives another product of our invention.

1,845 parts of the anhydrous It is to be understood that any or all of these reactions may be carried out under atmospheric,

Example 11 Condensation product of Example 2 98.0

subatmospheric, or superatmospheric pressure.

. Furthermore, various other factors and details may be changed within wide limits within the spirit of our invention. Our invention lies primarily in providing an application, of a known chemical reaction using our relatively pure halogen compounds to manufacture lubricating oils having extremely high viscosity indices. While we do not wish to claim the old processes, we do wish to claim all novelty inherent in our processes. as broadly as the state of the art permits.

If desired, our product may be prepared in such a manner as to leave some residual halogen. This.

halogen will remain in the aliphatic part of the ether molecule. For example, we may condense one molecular proportion of a relatively pure dichlorwax with one or 1.5 molecular propor-r tions of a metal phenolate or alcoholate. Or we may cause the condensation to proceed so as to remove halogencompletely from the aliphatic part of the ether but use a halogen-bearing aromatic hydroxy compound such as p-chlorobenzyl alcohol," o-chlorphenol or the like. If desired, a halogen-free condensation product may 'be halogenated to obtain a halogen-bearing lubricating oil. Any of these halogen-bearing products have superior lubricating properties, particularly in film strength as compared to the halogen-free lubricating oil.

Other elements such as sulfur, nitrogen or phosphorus may be present in our lubricating oil molecule. For the former purpose we'may produce high viscosity index lubricating oils of great economic value.

' Tin phenylstearate Triphenyl phosphite 1.0 Chlorodiphenylene oxide.. 1.0

Erample 12 Condensation product of sodium thiocresolate and monochlor wax 99.0 Methyl dichlorostearate 1.0

Example 13 Condensation product of Example 2 97.8 Solution of 25 percent naphthalene-chlorwax condensation product ,in- 75 percent of bright stock Sulfurized'methyl esters of corn oil acids";

EwampleM Cresoxywax (condensation product of Exam- -ple'2) I 75.0 Condensation product of sodium thionaphtholate and monochlor wax 25.0

Example 15 Cresoxy w 18.0

Condensation product of sodium B-hydroxyquinolinate with dichlor wax.-. 80.0

Sulfurized methyl linoleate s 0.2

Methyl dichlorostearate 1.8-

' It will be seen that we have accomplished the purpose of our invention; namely, to utilize petroleum hydrocarbons of low economic value to It will be understood that certain features and sub-combinations are of utility and may be emdeparting from thespi-ritof our invention.

ployed without reference to other features and subcombinations. This is contemplated by'and is within the scope of our claims. It is further obvious that various changes may be made in details within the scope of our claims without It is.

- therefore, to be understood that our invention use substituted reagents in the condensation such ,v

as p-nitrophenol, 2-chlor-3 amino-pentacosane, l-mercaptonaphthyl disulfide, hydroxyphenyl diphenyl phosphate, o-hydroxyphenyl diamylphosphine and the like. The finished lubricating product may be so made that it will contain from 0.2 to 20% by weight of one of the halogens, sulfur, nitrogen, phosphorus or combinations of two Generally quantities ranging or more of these. I from only 0.2 to 5.0% of these elements are conis not to be limited to the specific details shown and described. 7

Having thus described our invention, we claim: ,1. A lubricating oil having a viscosity index of over- 90 comprising principally an ether of the type ROR' where R is a high-molecular weight aliphatic radical having at least: 13 carbon atoms and R is an' organic radical containing at leastone cyclic nucleus.

tained in the lubricant.- We may add from 0.5 to 20% of other oxygenbearing organic compounds, halogen-containing or halogen-free, such as diphenylene oxide, chlorodiphenylene oxide, chlorinated diphenyls, smethyl dichlorostearate, benzyl sulfide, tricresyl phosphate, tri (2 -ethylhexylphenyll phosphite, benzyl sulfone, sulfurized methyl linoleate, diamyl' xanthate, lauryl thiocyanate and the like. Furthermore, we may add various metallic compounds such as chromium oleate, tetra-phenyl lead, aluminum naphthenate, calcium cetyl 3-isopropyl-6-methy1-3,6- endoethylene-4-tetrahydro phthalate, tin octadecyl phthalate, and the like. Examples of some of these blends are:

Example 10 n Percent Condensation product of Example 2 90.0

Sulfurized methyl linoleate (10% S) 10.0

2. A lubricating oil having a'viscosity indexof over 90 comprising principally a mixed cyclicalkyl ether with at least 13 carbon alkyl radical,

3. A lubricating oil v ove'g90 com prising principally a high molecular weight alkyl etheroi a phenolin which the allphatic radical containsatleast 13 carbon atoms.

v4. A lubricating oil graying a viscosity index of.

atoms in the oyer 90 comprising. principally a high molecular weight alkyl ether of a phenol inwhich the aliphatic radical contains at least 1%:

type ROR' where.,R is a high molecular weight aliphatic radical having. at least 13 carbon atoms and R is the. radical of a cyclic hydroxy com- Pound. I 6. A lubricating oil having a viscosity index of I arbon atoms. 5. A lubricating oil having a viscosity index of over: comprising principally an ether of the having a viscosity indexof over 90 comprising principally an alkylether" of 1 an aromatic hydroxy compound in whichthe aliphatic radical contains at least 13 carbon atoms.

,I h If '1'. A lubricating oil having a viscosity index of over 90 comprising principally an alkyl ether or a. substituted aromatic hydroxy compound in 9. A process for the production or lubricating oils having viscosity indices of over 90 comprising the steps of halogenating paraflin hydrocarbons whose monochloro derivatives melt lower than the hydrocarbons themselves, separating the mono, (11-, and polyhalogenated 'mrdrocarbons from each other and from unhalogenated hydro carbons and sepamtelyreplacing the halogen of each of the said relatively pure halogenated hydrocarbons by means of a. metal derivative '01 a cyclic hydroxy compound. 10. A process for the manufacture of lubricating oils having ,viscosity indices 01 over 90 comprising the steps oi halogenating paraflin hydrocarbons whose monochloro derivatives melt lower than the hydrocarbons themselves, separating the ii. A ifor the production a: lubricatin oils having viscosity indices oi over 90 comprising mono di-, and polyhalogenated hydrocarbons from each other and from unhalogenated hydro carbons and separately replacing the halogen of each of the said relatively purehalogenated hy- 30 drocar-bons by means of a metal phenola'te'.

the steps of halogenatin'g paraflin hydrocarbons whose monochloro-derivatives melt lowenthan the hydrocarbons themselves, separating the mono-, di-, and polyhalogenated hydrocarbons from each other and i'rom-unhalogenated hydrocarbons and separately replacing the halogen of each of the said relatively pure halogenated hyv dr'ocarbons by means of a metal derivative of anaromatic alcohol.

12. A'prccess for the production of lubricating oils having viscosity indices of over 90 comprising the stems of halogenating paramn hydrocarbons whose monochloro derivatives .m'elt lower than the hydrocarbons themselves, separating the mono-, di-, and polyhalogenatedhydrocarbons from each other and from unhalogenated hydrocarbons and separately replacing the halogen of each 0! the said relatively pure halogenated hy .drocarbons by means of a cyclic alcohol. a

' 13. A lubricating oil having'a viscosity index of over 90 comprising principally an ether ot the type ROR' where R is a high molecular weight aliphatic radical having atleast 13 carbon atoms and'R' is an organic radical containing at least one aromatic nucleus. .7

LLOYD L. DAVIS. BERT. H. Lm'COLN'; GORDON D. BYRKIT. 

